O-benzylcaryachine | 151832-60-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: O-benzylcaryachine
• 英文别名: (1S,12S)-15-methoxy-20-methyl-16-phenylmethoxy-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene
• CAS: 151832-60-9
• 化学式: C₂₆H₂₅NO₄
• 分子量: 415.489
• InChiKey: HDBAKKBDLXKEAF-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-benzylcaryachine 在 palladium on activated charcoal 氢气 、 C.I.酸性橙108 作用下， 以 乙醇 为溶剂， 25.0~160.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 N-propylnorcaryachine
  参考文献：
  名称：

  Preparation of N-Alkylnorpavines via Competitive N-Dealkylation of Quaternary Pavines

  摘要：

  N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl > allyl > Me > Et > Pr-n greater than or equal to (n)Bu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines.

  DOI：

  10.3987/com-96-7400
• 作为产物：
  描述：

  在 C.I.酸性橙108 作用下， 反应 3.0h， 以98.5%的产率得到O-benzylcaryachine
  参考文献：
  名称：

  Preparation of N-Alkylnorpavines via Competitive N-Dealkylation of Quaternary Pavines

  摘要：

  N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl > allyl > Me > Et > Pr-n greater than or equal to (n)Bu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines.

  DOI：

  10.3987/com-96-7400

文献信息

• Lee, Shoei-Sheng; Liu, Yi-Chu; CHang, Shu-Hwei, Heterocycles, 1993, vol. 36, # 9, p. 1971 - 1974
  作者：Lee, Shoei-Sheng、Liu, Yi-Chu、CHang, Shu-Hwei、Chen, Chung-Hsiung

  DOI：——

  日期：——
• Lee, Shoei-Sheng; Liu, Yi-Chu; CHang, Shu-Hwei, Heterocycles, <hi>1993</hi>, vol. 36, # 9, p. 1971 - 1974
  作者：Lee, Shoei-Sheng、Liu, Yi-Chu、CHang, Shu-Hwei、Chen, Chung-Hsiung

  DOI：——

  日期：——